My Favourite Caribbean Island


Shoal Bay,  Anguilla
Shoal Bay, Anguilla

I have this theory that I was switched at birth: I’ve got a Caribbean soul in a Canadian body.

Even if it’s only a theory, after last winter I’m ultra-sympathetic to those of the Caribbean diaspora who have settled in Canada and I’m wondering why I haven’t yet sold the house, bought a yacht and sailed into the Antillean sunset – rum punch in hand.

But where would I go? i.e.) what’s my favourite Caribbean island?

Depends on what you’re into.

These are no mere semantics on my part. I talk to people all the time about the Caribbean and I am always surprised at their takes and impressions. Someone tells me their favourite and it’s not even a top ten for me. I mention that perfect getaway and they tell me how much they hated it.

So you gotta know what you want.

Best islands for food are Sint Maarten (and its French neighbor St. Martin) and Barbados. Both are sufficiently sophisticated that they have a wide range of great restaurants (Grand Case Beach in St. Martin is a whole smorgasbord of great spots to dine), while Anguilla and St. Barth’s would make the list of finalists (for good reason, both are considered hideaways of the rich and famous; superior and diverse dining options are part of that equation). The only problem with the latter two is the fact that you might be maxing out your plastic for your entrée. St. Lucia’s also got some superb eateries – from mountain top tables to a hideaway literally on the water (it’s built on stilts).

But how do you work off those post-gourmet calories?

Try hiking – particularly on Grenada or St. Lucia. Gorgeous rainforest and mountain trails on both islands – some paths in Grenada are downright terrifying, some head to gorgeous waterfalls. I’m also hearing that Dominica is really well known for both major hiking trails and its sheer beauty.

Might not burn off as many calories if you’d prefer sea kayaking or snorkeling but they’re still Caribbean must-dos. One must-do kayak adventure is on St. Croix – a nighttime excursion through a mangrove lagoon.

My favourite place to snorkel is in Tobago Cays in the Grenadines, but USVI has some great spots – actual underwater trails on St. John. Nonsuch Bay in Antigua has an excellent barrier reef with a multitude of rainbow-hued fish and some good coral – and you can never go wrong in the Cayman Islands (also numero uno for divers).

Since I prefer history to hiking I lean toward forts and the like rather than class-five trails. Brimstone Hill on St. Kitt’s  is a gorgeous and imposing fortress in great shape, though they haven’t done a ton in terms of interpretive displays. Same for the fortress at Puerto Plata, though it’s worth a visit if you are in the area. Same for the fortifications on St. Vincent – a bit of history and killer views of the southern Caribbean.

Fort Christiansvaern, St. Croix, U.S.V.I.
Old Danish Customs House, St. Croix, U.S.V.I.

Coolest forts are on St. Croix in the USVI – one’s cherry red and the other is yellow, but when it comes down to living history Antigua tops the list. Spend time in English Harbour, a working Georgian dockyard. Check out the excellent museum then stroll out to the ruins of a fort, then head skyward for the Dow Interpretive Centre overlooking Nelson’s Dockyard.

Antigua gets another “best” award too, if you’re a beach bum (which I am).  Here you can find amber sand and beach restaurants without equal, isolated beaches of white sand, some accessible and some you have to work to find.  Spend a year in Antigua and you can do a different beach every day.

Anguilla probably ties Antigua for best beaches.  Here’s a telling irony: Shoal Bay is rated one of the world’s top and it’s not even my favourite on the island. (That’s two nods to Anguilla so far – maybe we’re on to something here.)

A couple of other places should go on your beach bucket list too. Seven mile beach, Grand Cayman. Absolutely spectacular. Crane Beach in Barbados. The Costa Dorada in D.R.. Negril in Jamaica – people-watching, rudimentary beach bars with that island vibe (though last time down I noticed they’re losing a bit of sand). Pinney’s Beach on Nevis has amazing views, delightful sand and a couple of great restaurants, while Orient Beach on St. Martin is one of the best people-watching beaches in the Caribbean. I haven’t even mentioned some other sand-swathed favourites, but you’ll have to discover them yourself. I don’t want them crowded with tourists on my next visit.

7 Mile Beach, Grand Cayman
7 Mile Beach, Grand Cayman

Which brings me back to the initial question.

Forget about the Caribbean. Forget about uncovering my favourite island.

Because if I tell you and you decide to check it out I may not get a seat on the plane.

And we certainly don’t want that to happen.

Do we?

8 Responses

  1. keith

    beautiful! Hope your spot opens up at LSYC soon.

  2. keith

    beautiful and well said! Hope your spot opens up at LSYC soon.

    • Mark Stevens, photos by Sharon Matthews-Stevens

      Thanks for this, Keith. Of course I never mentioned my favourite island for sailing. That’s gotta be BVI’s or the Grenadines.

  3. Paul Kandarian

    I’ve seen some of these and agree, but mostly about what the criteria is, whatever it is that floats your literal boat. My two faves are Petit St. Vincent, with which you are decidedly familiar, and Guana ISland in the BVI. But then again, every new place I visit is the next place I’d love to call home. I’m fickle that way, just a travel whore, content to put sandy feet up wherever they may be…:)

  4. Laura Byrne Paquet

    Oooh, I loved Grand Case! I could have easily spent a whole week there, just eating. (Then, of course, I would have had to head to Grenada for a week of hiking…)

    • Mark Stevens

      Conversely, Laura, you COULD head over to Anguilla and eat some more! Great restaurants there too. (Thanks for responding btw)

  5. Doreen Pendgracs

    Great round-up, Mark. I agree. Each island of the Caribbean has its own distinct personality, and I always tell people that they have to know what they’d like in the island experience before I would recommend one island over the other. I haven’t been to them ALL yet, but I’m working on it!

    • Mark Stevens, photos by Sharon Matthews-Stevens

      Hey Doreen – thanks for this. So here’s a chance for YOU to weigh in! Which Caribbean island (if any) produce the best cocoa? I do remember visiting a cocoa plantation last year in Tobago and wondered at the time if you’d ever done it.